2,6-Lutidine → 1-(Quinolin-6-ylmethyl)-1H-[1,2,3]triazolo[4,5-b]pyrazine-6-carbaldehyde

HRID 456140Notes

Reaction equation

HRID 456140 reaction equation
[CH:1]([C:3]1[N:8]=[C:7]2[N:9]([CH2:12][C:13]3[CH:14]=[C:15]4[C:20](=[CH:21][CH:22]=3)[N:19]=[CH:18][CH:17]=[CH:16]4)[N:10]=[N:11][C:6]2=[N:5][CH:4]=1)=C.CC1C=CC=C(C)N=1.I([O-])(=O)(=O)=[O:32].[Na+]>O.O1CCOCC1.[Os](=O)(=O)(=O)=O>[N:19]1[C:20]2[C:15](=[CH:14][C:13]([CH2:12][N:9]3[C:7]4=[N:8][C:3]([CH:1]=[O:32])=[CH:4][N:5]=[C:6]4[N:11]=[N:10]3)=[CH:22][CH:21]=2)[CH:16]=[CH:17][CH:18]=1

Participants

7

Reactant 3

HCID 79372,6-LutidineHCID 23667635Sodium periodateHCID 593418146-((6-Vinyl-1H-[1,2,3]triazolo[4,5-b]pyrazin-1-yl)methyl)quinoline

Product 1

HCID 866520351-(Quinolin-6-ylmethyl)-1H-[1,2,3]triazolo[4,5-b]pyrazine-6-carbaldehydeYield 2,233.8%

Reagents, catalysts & solvents 3

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To a mixture of 6-((6-vinyl-1H-[1,2,3]triazolo[4,5-b]pyrazin-1-yl)methyl)quinoline (100 mg, 0.347 mmol) and 2,6-dimethylpyridine (74.3 mg, 0.694 mmol), was added a solution of osmium(VIII) oxide (297 mg, 1.387 mmol) in H2O (1.333 mL), followed by a solution of sodium periodate (88 mg, 6.94 μmol) in 1,4-Dioxane (4 ml). The reaction mixture was stirred at rt for 10 h. The solvents was removed in vacuo and DCM was added to dilute the residue. The resulting solution was washed with saturated NaHCO3, NH4Cl and brine. The organic layer was separated, dried over Na2SO4, and concentrated to give a crude product, which was purified with Analogix gel silica (Hexanes:EA) to afford 45 mg of title compound in 43% yield. LCMS (method B): [MH]+=291, tR=1.00 min.

Workup

  1. customThe solvents was removed in vacuo and DCM
  2. additionwas added
  3. additionto dilute the residue
  4. washThe resulting solution was washed with saturated NaHCO3, NH4Cl and brine
  5. customThe organic layer was separated
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated
  8. customto give a crude product, which
  9. customwas purified with Analogix gel silica (Hexanes:EA)

Sources & evidence

ORD record
ord-788220e632784a09bf31297138bb8ce1
Source dataset
uspto-grants-2013_07
Patent number
US08497368B2

Reaction notes

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